Antioxidant



Patented MayJ 7, v v

.. sim e V Arthur WiSloan, Akron, Ohio, assignor'to The B; F, Goodrich Company, New York, N. Y., a" corporation of New York a 1N0 Drawing. Appntaiuintmsg 1933,

H I p 16 Claims. This invention relates tofl the. art of preserv ing rubber, fatty oilsgpetrolegum products syn thetic plastics-and like organic materials against unduly rapid deterioration-(inc te, oxidation and the like. .,r s

, This invention, in brief ,lco'nsists in-treating the rubber or other organic "material with a'member of a class of compounds which'may be c iesdrogen or hydrocarbon groups.

, varomatic nuclei, and X- and! are, eith'erfhy h. For. example, the following ,compoundsgare typical nembers of theclass of anti-.oxidantsjdescribed above: p-amino pfmethylami'io diphenylmethane; p,p di(methylamino) diphenylmethane; p-amino pdimethylamin'o diphenylmethane; p-methylamino pdimethylamino diphenylmethane; tetramethyll p',p"c liarninoi diphenylmethane; P,l1 di(methyl amino) dio-tolylmethane; di(metliylamino dinaphthyl. methane;

plp ,di (nietliylamino) diphenyl m'et hyl methane;

1 ,1 di'(methylamino) diphenyldimethyl meth ane; p,p di(methylamino) triphenylimethaneg p',p di methylamino itetraphenyl methane; p,p' di(methylamino) difibiplrienyl) methane; tetramethyl lip diaminotriphenyl methane} tetrarnethyl RP, diamlno diplienyldimethyl methane; tetramethyl 'diamino dinaphthyl methane; as Well as the corresponding "compounds substituted in the ortho, meta orother positionsand com,-

pounds in which the methyl groups are replaced by other aliphatic groups such, as ethyl, propyl, butyl; amyl, hexyhheptyl zetclg either straight or branchedchain and even groups such as cyclopentyl, cyclohexyl, benzyl and phenyl-ethyl groups, which, although" not strictly aliphatic in 'nature, undergo the characteristic reactions of and conier upon their compounds essentially the same properties as purely aliphatic groups. Any of the above-enumerated compounds may be used with good effect to retard the deterioration of rubber or other like organic substanc es,-preferably in moderately small proportions, say from p 0.1- to 5 per cent. s t

As a specific example oi? one embodiment of the invention of this application, a rubber composition is prepared containing, blended plantation' rubber 100" parts by weight,v sulphur 5.5 parts, zinc oxide 30 parts, gas black 46 parts, mineral rubber 10 parts, palm oil 5 parts, and

hexamethylene tetramine 0.75 part. One por tlon of this composition is used as av control,

while another portion is further mixedwithi Oil-l6 part by weight (0.5% of the composition) .of

I :tetramethyl psi'diarnin o 't riphenyl methane. *They have the general a After vulcanization in a press, for 45 minutes at 294 F. to produce an optimum cure, it is found that the composition containing the anti-oxidant deteriorates only approximately one-half as .fast

7 as the control composition when subjectedto an accelerated.- aging test such as the G eeroven test.

NT 9F Flo j l It is to be understood that the term treating isem'ployed in the appended claims ma generic sense to include'eitherthe incorporation of ,the anti-oxidants into th'erubbenorthe like by mixing them into the said material while it'is in a plastic or fluid condition," orfby applying them tothe surface of a solid mass thereof as a paste, powder or solution. The term rubber is likewisef employed in the claimsin a generic senseto include caoutchouc, both natural and synthetic, balata,'gutta percha, rubber isomers andlike products, whether or not admixed with,

agents. V l a While I have h'er in disclosed certain preferred manner'sof performing my invention, 1 donot thereby desire'or intendtolimit myself solely thereto, for, as hitherto stated, the precise pro,- portions of the materials utilized mayv be'varied fillers, pigments, or vulcanizing' or accelerating and other materials having equivalent chemical properties, may be employed if desired without departing from the spirit and scope of the invention as. defined in'the appended clair ns.

This application is a continuation in.,part of mybo-pnding application Serial No. 301,423

filed August '22, 1928.

I claim: 7 V I.

1. The method of preserving rubber which comprises treating rubber with a substance having the general formula A R-X-a-A' wherein A and A represent-amino groups, R

and R represent aromatic nuclei and X represents a methylene 'or hydrocarbon substituted methylene group, and at least one of the groups A and A contains an aliphatic hydrocarbon substituent. T a Y '7 groups, and Y represents a hydrocarbon sub 2. The method of preserving rubber which comprises treating rubber with a substance having the general formula wherein A and A represent aliphatic hydro carbon substitutedamino groups, R and Rrepresent arylene groups, and X represents a methylene group. p 1 r 3.- The method. of preserving rubber which comprises treating rubber with a substance hav' ing the general formula -wherein A and. A represent fallryl substituted amino groups, R and R represent arylene stituent. I

4. The method of preserving rubber which comprises treating rubber with a substance having thegeneral formula wherein'A and; A represent alkyl substituted amino groups and R and, R represent aromatic,

nuclei.

5..The method of preservingrubber which comprises treating rubber with a substance having" the general formula wherein A and A represent ,diakyl aminogroups,

R and R represent aromatic nuclei, and. Y representsahydrocarbon substituent.

V 6. The method voi preserving, rubber which,

comprises treating rubber with 'tetramethyl diamino diphenyl methane;

'I. The method of preserving comprises treating v} diar'nino triphenyl methane.

8. A composition comprising rubber and a substance having the general formula A- -X-RFA" wherein A and A represent amino groups R and R represent aromatic nuclei and X repree sents a methylene or hydrocarbon substituted methylene group, and at least 0116 0]? the groups A and A contains 'anfaliphatic hydrocarbon groups, and Y rubber with tetramethyl,

wherein A and A represent alkyl substituted amino groups, R and. R represent arylene groups, and Y represents a hydrocarbon substituent. 1

11. A composition comprising rubber and a substance having the general formula wherein A and A represent aliphatic hydrocarbon substituted amino groups, R and R represent arylene groups, and X represents a methylene group. p V

12. 'A' composition :comprising rubber and a substance having the general formula wherein A and A" represent alkyl substituted amino groups, R and Rf represent phenylene represents a hydrocarbon substituent; 7 Y

13.-A composition comprising rubber and a substance having the general formula A-R-CHZ-RHA' wherein A and A' representalkyl'substituted amino groups and R and R represent aromatic nuclei,

14. A composition comprising rubber and a substance having the general formula A-R-C-R'A' Yv wherein" A and. A "represent dialkyl amino groupsyR and R" represent aromatic nuclei,

i and-Y represents ahydrocarbon substituent. rubber wh ch 15. The method'bf preserving rubber which 7 comprises vulcanizing a mixture containing rubber, sulphur, an active organic accelerator of vulcanization, and. a substance having the general formula' v A-R-X-R A wherein A and A :represent amino groups, R and. R represent aryl groups and X represents a methylene group or'hydrocarbon substituteol methylene group, and at least one of the groups 'A and A contains an aliphatic hydrocarbon substituent.

16. The methodfof preserving rubber which comprises vulcanizirig a mixture containing rubber, sulphur, an activeoorganic accelerator of vulcanization, and a substance having the general formula r V V V "AR- X Ri- -A' wherein A and A represent alkyl substituted amino groups, R and. R represent arylene groups, anolX represents a methylene group.

7 ARTHUR W. SLOAN. 

